


Sensational

by Sashataakheru



Series: You Look So Fine - Crossdressing!Greg fics [2]
Category: Taskmaster (UK TV) RPF
Genre: Age Play, Body Hair, Comfort blanket, Community: seasonofkink, Crossdressing, M/M, Multi, Pampering, Pyjamas, Self-Love, Sensation Play, Shaving, Sleepovers, Soft Toys, Teasing, Threesome, fabrics, personal care, shaving/waxing, slumber parties
Language: English
Status: Completed
Published: 2018-08-20
Updated: 2018-08-20
Packaged: 2019-06-30 06:04:52
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,877
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15745776
Author URL: https://archiveofourown.org/users/Sashataakheru/pseuds/Sashataakheru
Summary: In which, Roisin finally convinces Greg to shave all his body hair off, and just for a moment, experience wearing a dress properly so that Alex can see what his master looks like as a woman.





	Sensational

**Author's Note:**

> Written for the prompt 'shaving/waxing' for Season of Kink 2018. My card and fills are [here](https://3evilmuses.dreamwidth.org/82357.html).
> 
> You might not have wanted more crossdressing!Greg fic, but my Muses sure as shit did. Final-ish smexing part to come, unless I decide to write what happens in the middle as well. Also, apologies for the fic-spam, but this bingo card is on a deadline and I am behind where I want to be right now.

“I’ve always wanted to do this for you,” Roisin said as she lathered his arm with shaving foam. “I wanted to be the one who helped you look beautiful, cos let’s face it, you’d have struggled on your own.”  
  
“How wonderful to hear how little faith you have in me,” Greg said, gazing at his arm as Roisin slowly drew the razor across his skin, leaving a smooth trail in its wake. “You sure I need to do this? I’m sure I looked fine last time.”  
  
“If you think the only thing you told me was about that dress and nothing more, you’re mistaken, pal. You told me all the things you wanted to do, that you felt you could only let yourself do as a woman, and you know what I’m like, I remembered all that shit, because it was you, because you wanted me to know. I’ve been planning a night like this for years. I wanted to make sure you felt safe and loved and allowed to just be you, to do all those things and pamper yourself, yeah? So I could be the one to make you look beautiful. I mean, you don’t need to do your whole body, sure, but at least lemme do your chest, arms, and legs, then maybe you’ll feel better about it. And it’ll make the fabric feel so nice on your skin, trust me. You don’t need to wear the gown though, I got you a little slinky camisole and a dressing gown made of the same fabric, cos that’s what you want for a slumber party, yeah? And you did say you wanted to look sexy in a dress,” Roisin said.  
  
Greg didn’t really know what to say to that. He was only just beginning to realise she wasn’t just being a supportive friend, but was also really into it as much as he was. She _wanted_ to see him as a woman, she wanted _him_ as a woman. He never thought anyone would find him attractive in drag, but the fact she did had thrown him, because she’d never been interested in women as far as he was aware.  
  
“Are you just going to keep buying clothes for me? So you can dress me up? What on earth did I do to deserve you, Rosh?” Greg said, not sure what else to say.  
  
“I just want you to be happy, Greg, that’s all I’ve ever wanted for you. If that means buying special clothes for you that you’d never buy for yourself, so be it. Now, how much of your body should I shave? Because I want you to be comfortable with this,” Roisin said.  
  
“Are you sure no one will notice? Because that’s what stopped me before. Surely people will notice,” Greg said, hesitant, as she washed his now-smooth arm.  
  
“It’s only hair, Greg, it’ll grow back if you really hate it that much. Besides, no one will notice unless you point it out. Just wear long sleeves if you really want to hide it,” Roisin said.  
  
Greg could tell he wasn’t going to win this one, and let her get on with it. It wasn’t like she wanted him to go out in the world like this, and if all else fails, perhaps he’d just say he lost a bet if anyone asked.  
  
At least Roisin seemed to be enjoying herself. She took her time with it, stopping every now and then to kiss him, or tease him, or get him to touch his skin to feel how smooth it now was. It wasn’t going to be smooth like hers, but it still felt weird. He wasn’t sure it was more sensitive, or if he was just paying more attention to the way her fingers traced circles on his arms as she smiled at him.  
  
In some ways, this felt like the most intimate thing they’d ever done together. Here she was, taking such tender care of his whole body, and he was sure she didn’t need to be so slow and gentle with the razor, but it did make his spine tingle, and he found he quite enjoyed that. She did too. And if she added in some gentle massage as she went, well, he wasn’t going to complain, particularly not when she got to his feet, and for a while, he almost forgot what they were meant to be doing.  
  
He wasn’t sure he wanted her to shave his genitals when she’d first offered this, but it was hard to say no when she kept stroking him and making him feel real good. It’d been a while since they’d last slept together, and he always missed her touch. At least they had more time now, and she was taking full advantage of that. The night was still young, Alex was – as far as he could remember – still doing things in the kitchen, but he might also be waiting for them, too. He hadn’t wanted Alex here, not if Roisin was going to dress him up, but she talked him round, and besides, Alex wanted to see him in his dress, and Greg just couldn’t say no, not when he looked at him with his big blue eyes, touched his arm in just the right way that told him he didn’t care, promised he would do whatever he wanted, he would leave if he needed him to, if he didn’t feel comfortable.  
  
But he didn’t want Alex to go. Now, all he was thinking about was how good it might feel to have Alex run his hands over his body while he was wearing that dress, to let his boy enjoy those sensations. He’d never get Alex to shave his body, or wear a dress, but that didn’t matter. Perhaps, just for one night, he could let Alex serve a Queen, rather than his Daddy.  
  
“Do you want me to get Alex? So he can see how you look now?” Roisin said once she was done.  
  
“What, before I’m all dressed up like a queen? Are you kidding me? No, he can wait till we’re properly done, then he can see me,” Greg said.  
  
“I didn’t know you wanted to be a queen, Greg. I thought you were all about being king,” Roisin said.  
  
Greg waved off her remarks. “Oh, it was something Alex said, you know, after you gave me the dress? I told you he came round anyway, and he saw me. So of course I had to tell him, didn’t I? He said maybe there’s a castle in Spain where I can be a queen, and have parties, and he can be my knight in shining armour and defend my honour or something. It was the most adorable thing I’ve heard him say, and I kinda want to do it, you know? I’m sure we can find a cheap run-down castle in Spain somewhere, right? Imagine how good that would be? We could be queens together, and Alex could be our lady-in-waiting. His kids would love living in a castle, right?”  
  
“Oi, if you’re being queen, I’ll be king then. Someone’s gotta wear the trousers, right? But at least I know what outfit I’m going to get you next. Then you really will be a queen, I promise. I’ll get you a crown and everything,” Roisin said with a grin.  
  
“I’m still not sure if telling you my deepest darkest secrets about dresses was the best idea in the world, you know. But at least it was you and not someone else, so I can’t be mad at you for that,” Greg said. “So, is that everything then? Can I get my sexy dress on now?”  
  
Roisin handed him a bottle of body lotion that claimed to smell like rose and geranium. Greg was sceptical. “Put that on, you’ll smell so pretty. And you can see how you feel now. You do that, and I’ll get the sexy dress all ready for you, yeah?”  
  
“Yeah, alright,” Greg said, figuring he was too committed now to not keep going with her plans. He watched her leave, and was a little thankful for being alone at last, if only for a moment.  
  
He hadn’t wanted to admit she’d been right, that he had wanted this partly so he could pamper himself. That much he had figured out about why he loved the dress so much. And now, he had smooth skin, and he hadn’t expected it to feel as good as it did as he began to rub the lotion into his skin. It did smell like geranium, at the very least, though he wasn’t sure it was his favourite scent of all time. It didn’t take away any of the pleasure of it, and he felt he was getting to know his body all over again in a new way.  
  
He’d never really taken that much care of his skin, if he was being honest. It was what it was now, and the damage was done. It was never going to be perfectly young and smooth as if he was a kid again, but he had to admit, it did feel a little better after he’d put the body lotion on. It was meant to be moisturising, after all, and without the hair, he felt it almost made him feel younger. It certainly felt smoother, and softer, and perhaps he might do this again, if he could find a scent he actually liked, and just get to know his body again and take care of it. He’d never been very good at that, but maybe it was time to change that. Maybe that’s why this was happening now.  
  
He didn’t hear Roisin return until he was done, and he looked over to find her standing in the doorway, clearly enjoying the view.  
  
“Better?” she asked.  
  
“Yeah, better. That for me, is it?” Greg said, seeing the new dress hanging over her arm.  
  
She handed it to him. “Yeah, that’s it. Pale lavender, I thought, make it a bit softer, you know? The robe’s the same colour as the dress, with gold trim, because I know you want to be king, and purple and gold are royal colours, apparently. Maybe that’s why the dress was always purple for you. You always knew you were going to be king.”  
  
He had to smile as he slipped the camisole over his head. It was simple, but the sensation of the fabric on his bare skin was actually kind of incredible, and he was thankful Roisin talked him into shaving his body, just for that one moment of pleasure. He might’ve spent a moment just running his hands over his chest, just because he could, because the sensation of the fabric on his bare skin was more intense than he had expected. He hadn’t imagined shaving would change it that much, but apparently, he’d been wrong.  
  
“What’d you think?” Greg said once he’d straightened it out. It sat halfway down his thighs, perhaps shorter than he might have otherwise gone for, but he did quite like his legs, and he thought they looked good paired with the cami for once.  
  
“That was definitely the right colour. How’s the length? Is it long enough? I had to kind of guess, because I didn’t know how long you might want it. Is it too short? I feel like it’s too short,” Roisin said.  
  
“It might be a bit short, but does that really matter? It’s not like you care, and Alex won’t care. Besides, I’m not going to turn down a sexy number like this if it means you two can easily suck me off while we’re pretending to watch girly movies all night, yeah?” Greg said. “Cos, I mean, if you think for one moment we’re not going to end up having sex tonight, well, you’d be very wrong.”  
  
Roisin took that as an invitation to press against him as she slipped a hand under the dress and squeezed his cock. “Oh, that was always in the plans, don’t you worry about that. You did get the mirror out, right? So Alex can watch me fuck you in your pretty dress?”  
  
“It’s all ready to go. Chair, mirror, restraints, and I even got the cockring he asked for. You do remember what I told you about him, yeah? About what you can’t do to him? Otherwise, he’ll get in trouble, and then I’ll get in trouble, and then I’ll pass on that punishment to you for not fucking listening, yeah?” Greg said.  
  
Roisin knew, but did pretend to look disappointed. “Yeah, yeah, I know. I mean, I can still touch him, yeah? I can still touch your boyfriend, right?”  
  
“Yeah, you can touch him, just not fuck him. I mean it, Roisin. I don’t care how much you might fall in love with his cock, don’t fuck him. Only I know what you’re like, and I don’t want you getting him in trouble,” Greg said.  
  
“That’s what you get for falling in love with someone else’s boy, Greg. You go and deprive me of a perfectly good cock. But don’t worry, I’ll still show your boyfriend a good time,” Roisin said, undaunted.  
  
“I’m sure you will. And I don’t know why you keep calling him my boyfriend. You know more about our relationship than anyone else, and you’re still calling him my boyfriend? You know that’s not what he is to me,” Greg said.  
  
“What else do you want me to call him that won’t expose you? Do you want me to go around telling the world he’s your slave? He’s your little puppy dog? Like, I’m trying to protect you, Greg, and it’s not like you haven’t had boyfriends before either. No one’s going to think it’s weird, not for you,” Roisin said.  
  
“I mean, okay, that is true, but you still don’t need to call Alex my boyfriend when you’re talking to me though. We both know what he is. Save that for everyone else. I can assume that, for once in your life, you haven’t gone around telling the world who I’m sleeping with? Because unlike all the others, this one needs to be secret,” Greg said.  
  
“Have a bit more faith in me, man, I ain’t told no one. I know how to keep your secrets,” Roisin said. “Now, put your robe on and I’ll get your face done. I got another wig too, you might like it better. Then we can go and play with Alex, yeah?”  
  
Greg took the robe, appreciated that it was the same dark purple as the gown, and had the same gold braid trim. That did feel amazing to put on, and he was beginning to feel like he was a woman, or at least, dressed more like one. He let Roisin put some light make-up on, and that, along with the wig, completed the transformation. This wig was definitely better. Shorter, more of a straw blonde, he liked the way it sat around his face. Roisin’s hands gently stroking his chest, enjoying the sensation of that fabric against his smooth skin, stopped him lingering in front of the mirror to take in his appearance, not when her hands then threatened to slip under his dress again.  
  
“Come on, let’s go find Alex, I want him to see this, now that it’s all done,” Greg said.  
  
“Okay, here’s your bunny slippers, too. I thought you might want something other than heels for tonight,” Roisin said, bringing out one last gift.  
  
“You have really outdone yourself, Rosh, they’re absolutely hideous. I love them,” Greg said as he saw the ridiculously fluffy pink rabbit slippers, complete with nose, ears, whiskers, and the most sinister red eyes he’d ever seen on a pair of slippers before. They were, however, ridiculously comfortable, so he was willing to look past the psychotic rabbit eyes.  
  
“I thought you’d like them. Now, come on, your boy’s waiting for you,” Roisin said.  
  
She took his hand, and he followed her out to the lounge, where Alex was waiting for them. This would be the first time Alex had seen him all done up, and perhaps it might’ve been a more perfect moment save for the fact Alex was standing there awkwardly, dressed in a pink satin robe, looking like he wanted to run and hide and not be seen but wasn’t willing to disobey an order to wait for his master here. Greg gave Roisin a very pointed look.  
  
“What have you done to my boy, Roisin? Why’s he dressed like that?” Greg said, making a show of bringing Alex into his arms, away from her.  
  
“I thought that’s what you wanted. It’s meant to be a sleepover right? A girly night in? Isn’t that what you wanted?” Roisin said.  
  
Greg ignored her. “Alex, go and get into your pyjamas, you don’t have to wear that if you don’t want to.”  
  
“Yes, sir, thank you, sir,” Alex said, giving Greg a quick peck on the cheek before he scampered off.  
  
“I thought I’d told you to stop giving him orders like that. He’s my boy, not yours. If you want to own him too, you can sit down with his wife and negotiate your own contract, yeah? Keep your hands off him. When he gets back, you can apologise to him, and maybe I won’t let you touch him at all tonight, just to make a point,” Greg said.  
  
Roisin crossed her arms across her chest, but didn’t protest, knowing she’d been pushing her luck with Alex’s robe, even though it had been worth it to see him standing there blushing with embarrassment. Why he even still obeyed her, she didn’t know, but that was Greg’s problem to sort out, not hers.  
  
“Fine. But you can’t tell me he didn’t look cute in pink, though,” Roisin said.  
  
“You might find sissy boys a turn on, which would be out of character for you, let’s be honest, but that’s not what Alex is into at all. I’m the one who likes dresses, not him. If you’re going to keep on being part of this, we’re going to have to talk you through all his kinks, because I won’t have you just doing whatever you like with him. He doesn’t like that,” Greg said.  
  
“Spoil sport,” Roisin said, but she didn’t really mean it. “Sorry, Greg. I got a bit carried away. I mean, he’s alright with me being here, yeah? This isn’t weird for him?”  
  
“Why would he find it weird? He likes you, Rosh, he’s been all excited about tonight and what you’ve got planned. You fucked it up by putting him in a dress, because I know under that robe, you did put him in a little sexy dress, didn’t you, you monster,” Greg said.  
  
“Yeah, I did, sorry. I guess I just wanted us all to be dressed the same. I’ve never done one of these with a boy before, that’s not how they work. I should’ve asked him, hey?” Roisin said.  
  
“Yeah, you should’ve asked. I know you’re not my submissive, but just, when it comes to Alex, just listen to me, alright? He’s my responsibility, not yours, and unlike everything else I own, you aren’t just entitled to use him however you want, yeah?” Greg said.  
  
Alex returned then, before Roisin could answer, this time dressed in an adorable set of pyjamas with little teddy bears on it, his favourite toy rabbit tucked under one arm, and his blanket clutched in the other hand trailing behind him. Greg brought him into his arms, and gave him a hug, clearly recognising he needed one, and kissed the top of his head.  
  
“Feeling better now, Alex?” Greg said, looking down at him.  
  
Alex nodded. “Better, yes, sir. I’m sorry, I was meant to see you in your beautiful dress for the first time, and I’ve ruined the moment. But you do look lovely, sir. Thank you for sharing this with me, sir.”  
  
“Roisin ruined it for me, but thank you. Now, don’t you have something you need to say to Alex, Roisin?” Greg said.  
  
Roisin went over to Alex and knelt at his feet. She hadn’t been asked to kneel, but she did it anyway, feeling like it was the right way to apologise. “I’m sorry, Alex, for making you wear that dress. I should’ve asked if you wanted to wear it, and not just assumed you did. I hope we can still enjoy the night I planned for us, Greg said you were really looking forward to it.”  
  
“It’s okay, Roisin, I should’ve said something. But, I mean, if you wanted to get me some more boy pyjamas like this, I, well, I wouldn’t say no. I like ones with animals on them,” Alex said.  
  
Roisin had to smile as she got to her feet. “I’ll get you some pyjamas, ones you actually want. Maybe some with dolphins on them, yeah?”  
  
Alex smiled. “Dolphins would be lovely, thank you.”  
  
Alex brought her into a hug, all Roisin needed to know she’d been forgiven. “Alright, now go and see what a lovely job I did making your master all beautiful, yeah?”  
  
Alex turned to Greg, and took in his appearance properly this time. “I know you said you were going to do the whole thing, but I wasn’t expecting it to look this good. Well done, Roisin. He does look lovely.”  
  
“Thanks, Alex. I know this was a surprise to you, but he just wants to be beautiful,” Roisin said.  
  
“Oh, it’s okay, I don’t mind. I still wish he’d told me right from the start, but I can’t be angry at him when it makes him this happy,” Alex said.  
  
“Sometimes, Alex, I think you’re better to me than I really deserve. But I’m glad you like it. She shaved my body, too, this time. Feel how smooth I am now,” Greg said.  
  
Alex did notice it, but hadn’t wanted to say anything. Still, he appreciated the invitation to touch him, and it was a strange feeling, to feel how smooth his master’s skin now was. He took his time, knowing that’s what Greg wanted, and got to know him in this new form, where he was now wearing a short little dress, and a wig, and make-up. Alex studied him, touched him everywhere, caressed him gently, and convinced himself Greg was still his master, even dressed like this.  
  
“You look very nice, sir. She did a good job, sir,” Alex said.  
  
Greg couldn’t help bringing Alex’s hand between his legs, under the dress, the one place he hadn’t gone. “Do you like that? Does that feel good?”  
  
Alex hadn’t expected him to commit to it to that extent, but he could tell Greg was clearly enjoying his touch, and that just made him enjoy it too as he gently stroked him a few times.  
  
“You have been busy, sir. I’m assuming you’re not going to stop me slipping my hand up your skirt, are you, sir?” Alex asked.  
  
Greg had no intention of stopping him at all. “Of course not, that’s half the reason it’s so short. Now, I think it’s time we got this party started, don’t you?” 


End file.
